Synthesis And Property Of 3', 6'-bis (N, N-diphenylamino) Fluoran

The pressure&heat -sensitive dye is an important kind of functional dye, it is widely used in the production of pressure&heat -sensitive paper. As the third generation of pressure&heat-sensitive dye, fluoran compounds represented the tendency all over the world, the synthesis of a series of new fluoran dyes is significant. In addition, because of the special structure and fluorescent property, the fluoran dyes are widely applicated as tracers for lacatization of biological structures, quantifying analytes, analysis of cells by flow cytometry, measurement of the physiological states of cells, quantitative assays such as DNA sequencing, and other applications. It is a hotspot in the chemical and biological analysis field. For the purpose of improving thermal stabilit and prolonging the emission wavelength, a fluoran compound was designed and its synthesis and properties were studied in this present thesis.The intermediate 3-(N,N-diphenyl)aminephenol was synthesized from two different routes. First, the m-dihydroxybenzene and diphenylamine was catalyzed by 85% phosphoric acid at 220℃, the product was obtained, and the influencing factor of the reaction was examined. Second, the m-bromophenol was obtained from m-aminophenol by diazotization, and then it reacted with the diphenyl by Ullmann reation to give the product. Finally, the 3',6'-bis(N,N-diphenylamino)Fluoran was obtained from the 3-(N,N-diphenyl)aminephenol and phthalic anhydride at 180℃, the p-toluenesulfonic acid was used as a catalyst. The structure of the dye was comfirmed by IR,MS and 1HNMR.The optical spectrum and electrochemical properties were investigated. The UV-Vis showed that the conjugate degree of fluoran was enhanced by the introduction of phenyl group on the nitrogen of 3'and 6'position. The fluorescence spectra showed that the maximum emission wavelength is between 405nm~493nm. The voltammetry indicated that only a reduction peak was appears at -0.711V in dichloromethane.